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Article Dans Une Revue ACS Catalysis Année : 2021

Heterogenization of a Molecular Ni Catalyst within a Porous Macroligand for the Direct C-H Arylation of Heteroarenes

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Direct C–H functionalization catalyzed by a robust and recyclable heterogeneous catalyst is highly desirable for sustainable fine chemical synthesis. Bipyridine units covalently incorporated into the backbone of a porous organic polymer were used as a porous macroligand for the heterogenization of a molecular nickel catalyst. A controlled nickel loading within the porous macroligand is achieved, and the nickel coordination to the bipyridine (bpy) sites is assessed at the molecular level using IR and solid-state NMR spectroscopy. The heterogenized Ni-bpy catalyst was successfully applied to the direct and fully selective C2 arylation of benzothiophenes, thiophene, and selenophene, as well as for the arylation of free NH-indole. Recyclability of the catalyst was achieved by employing hydride activators to reach a cumulative turnover number of more than 300 after seven cycles of catalysis, which corresponds to a total productivity of 12 g of 2-phenylbenzothiophene, chosen as model target biaryl, per gram of catalyst.
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hal-03190555 , version 1 (05-07-2021)

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Yorck Mohr, Marcelo Alves-Favaro, Rémy Rajapaksha, Gaëlle Hisler, Alisa Ranscht, et al.. Heterogenization of a Molecular Ni Catalyst within a Porous Macroligand for the Direct C-H Arylation of Heteroarenes. ACS Catalysis, 2021, 11 (6), pp.3507-3515. ⟨10.1021/acscatal.1c00209⟩. ⟨hal-03190555⟩
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